re: What is the most you've ever been overdressed?

I always wear a suit to a wedding. If you have a bunch of people who wear jeans there, it's their fault for dressing like that, I'm dressed correctly in my suit.

Now for engagement parties and things like that, I usually wear a versatile set of clothing. Something that looks good with a coat and tie, just a coat, and taking the coat off. That way I fit in no matter what.

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For my first job interview for a YMCA summer camp counselor job I showed up wearing a tie and slacks.

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You can never be overdressed in a job interview IMO.

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I was actually told once that if the guy hadn't already known me, he wouldn't have offered me a job because I wore a suit after he told me that it was going to be a very casual interview

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That's a fricking stupid reason to not hire someone. Unless you're required to perform some kind of manual labor at the interview a suit should always be acceptable at an interview.

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I was actually told once that if the guy hadn't already known me, he wouldn't have offered me a job because I wore a suit after he told me that it was going to be a very casual interview

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Sounds like you don't listen and were inappropriately dressed.

Edit: that was kind of a dick thing to say. My bad.

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What if the only other person in a suit is the groom and it's a casual wedding?

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I've never been to a casual wedding. In fact I've only ever been to one wedding that wasn't in a church. If the groom is wearing a suit, then it doesn't matter if others are wearing a suit. Plus, I have "casual" suits (seersucker, tan, light grey).

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If the groom is wearing a suit, then it doesn't matter if others are wearing a suit. Plus, I have "casual" suits (seersucker, tan, light grey).

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what is the groom is wearing a casual suit?

You're never the most overdressed person in a room, everyone else is just underdressed.

Reminds me of one my favorite quotes from 30 Rock:

"Jack, why are you wearing a tux?"

"It's after 6 Lemon. What are we, farmers?

Every summer job interview I went to in college, I was overdressed. One time, the lady just flat out asked "why are you wearing that silly stuff?" because I was wearing suit pants and and a dress shirt.

The last summer job interview I went to, boy. It paid pretty good money ($20 an hour) for a summer job and I knew they wouldn't like that I'd only be available for like a month. So I went in a suit. Jeez, there were people who were wearing sandals and t-shirts. There was a rotund girl blarring loudly that her school was known for their "hoes".

One time freshmen year the fire alarm went off in the dorms and not wanting to look like a bum that was still in bed I put on my usual khakis, button-down and sweater and everyone else was in their jammies..